TW527337B - Alkene oligomerization process - Google Patents
Alkene oligomerization process Download PDFInfo
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- TW527337B TW527337B TW090113603A TW90113603A TW527337B TW 527337 B TW527337 B TW 527337B TW 090113603 A TW090113603 A TW 090113603A TW 90113603 A TW90113603 A TW 90113603A TW 527337 B TW527337 B TW 527337B
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- 150000001336 alkenes Chemical class 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000006384 oligomerization reaction Methods 0.000 title claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 58
- 239000010457 zeolite Substances 0.000 claims abstract description 38
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 46
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000011049 filling Methods 0.000 claims description 24
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 22
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 22
- 229930195733 hydrocarbon Natural products 0.000 claims description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 18
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 15
- 230000036571 hydration Effects 0.000 claims description 12
- 238000006703 hydration reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 10
- RGYAVZGBAJFMIZ-UHFFFAOYSA-N 2,3-dimethylhex-2-ene Chemical compound CCCC(C)=C(C)C RGYAVZGBAJFMIZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 230000002079 cooperative effect Effects 0.000 claims description 3
- 230000003606 oligomerizing effect Effects 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 230000006315 carbonylation Effects 0.000 claims description 2
- 238000005810 carbonylation reaction Methods 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 238000005194 fractionation Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 241001494479 Pecora Species 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 229910052722 tritium Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 description 48
- 239000013078 crystal Substances 0.000 description 18
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 18
- -1 H — ZSM-57 Chemical compound 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 9
- 239000001282 iso-butane Substances 0.000 description 9
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- 239000002808 molecular sieve Substances 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 238000005336 cracking Methods 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 229940069096 dodecene Drugs 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910000449 hafnium oxide Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PSABUFWDVWCFDP-UHFFFAOYSA-N 2,2-dimethylheptane Chemical compound CCCCCC(C)(C)C PSABUFWDVWCFDP-UHFFFAOYSA-N 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical compound CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 2
- WBRFDUJXCLCKPX-UHFFFAOYSA-N 2,3-dimethylheptane Chemical compound CCCCC(C)C(C)C WBRFDUJXCLCKPX-UHFFFAOYSA-N 0.000 description 2
- AUKVIBNBLXQNIZ-UHFFFAOYSA-N 2,4-dimethylheptane Chemical compound CCCC(C)CC(C)C AUKVIBNBLXQNIZ-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- KBPCCVWUMVGXGF-UHFFFAOYSA-N 2,6-dimethylheptane Chemical compound CC(C)CCCC(C)C KBPCCVWUMVGXGF-UHFFFAOYSA-N 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- ARWOOWBJJKVYOV-UHFFFAOYSA-N 3,3,4-trimethylhexane Chemical compound CCC(C)C(C)(C)CC ARWOOWBJJKVYOV-UHFFFAOYSA-N 0.000 description 2
- KUMXLFIBWFCMOJ-UHFFFAOYSA-N 3,3-dimethylhexane Chemical compound CCCC(C)(C)CC KUMXLFIBWFCMOJ-UHFFFAOYSA-N 0.000 description 2
- MAKRYGRRIKSDES-UHFFFAOYSA-N 3,4-dimethylheptane Chemical compound CCCC(C)C(C)CC MAKRYGRRIKSDES-UHFFFAOYSA-N 0.000 description 2
- RNTWWGNZUXGTAX-UHFFFAOYSA-N 3,4-dimethylhexane Chemical compound CCC(C)C(C)CC RNTWWGNZUXGTAX-UHFFFAOYSA-N 0.000 description 2
- DZJTZGHZAWTWGA-UHFFFAOYSA-N 3,5-dimethylheptane Chemical compound CCC(C)CC(C)CC DZJTZGHZAWTWGA-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 2
- SEEOMASXHIJCDV-UHFFFAOYSA-N 3-methyloctane Chemical compound CCCCCC(C)CC SEEOMASXHIJCDV-UHFFFAOYSA-N 0.000 description 2
- CHBAWFGIXDBEBT-UHFFFAOYSA-N 4-methylheptane Chemical compound CCCC(C)CCC CHBAWFGIXDBEBT-UHFFFAOYSA-N 0.000 description 2
- DOGIHOCMZJUJNR-UHFFFAOYSA-N 4-methyloctane Chemical compound CCCCC(C)CCC DOGIHOCMZJUJNR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- JXPOLSKBTUYKJB-UHFFFAOYSA-N xi-2,3-Dimethylhexane Chemical compound CCCC(C)C(C)C JXPOLSKBTUYKJB-UHFFFAOYSA-N 0.000 description 2
- 239000012690 zeolite precursor Substances 0.000 description 2
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- ACYHSTUWOQNWCX-UHFFFAOYSA-N 2,2,3-trimethylheptane Chemical compound CCCCC(C)C(C)(C)C ACYHSTUWOQNWCX-UHFFFAOYSA-N 0.000 description 1
- AFTPEBDOGXRMNQ-UHFFFAOYSA-N 2,2,4-Trimethylhexane Chemical compound CCC(C)CC(C)(C)C AFTPEBDOGXRMNQ-UHFFFAOYSA-N 0.000 description 1
- IIYGOARYARWJBO-UHFFFAOYSA-N 2,2,4-trimethylheptane Chemical compound CCCC(C)CC(C)(C)C IIYGOARYARWJBO-UHFFFAOYSA-N 0.000 description 1
- HHOSMYBYIHNXNO-UHFFFAOYSA-N 2,2,5-trimethylhexane Chemical compound CC(C)CCC(C)(C)C HHOSMYBYIHNXNO-UHFFFAOYSA-N 0.000 description 1
- QACXEXNKLFWKLK-UHFFFAOYSA-N 2,3,3-trimethylheptane Chemical compound CCCCC(C)(C)C(C)C QACXEXNKLFWKLK-UHFFFAOYSA-N 0.000 description 1
- DJYSEQMMCZAKGT-UHFFFAOYSA-N 2,3,3-trimethylhexane Chemical compound CCCC(C)(C)C(C)C DJYSEQMMCZAKGT-UHFFFAOYSA-N 0.000 description 1
- UVVYAKOLFKEZEE-UHFFFAOYSA-N 2,3,4-trimethylheptane Chemical compound CCCC(C)C(C)C(C)C UVVYAKOLFKEZEE-UHFFFAOYSA-N 0.000 description 1
- HQZHQNKZOYIKQC-UHFFFAOYSA-N 2,5-dimethylheptane Chemical compound CCC(C)CCC(C)C HQZHQNKZOYIKQC-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- OBCGEYFMJYXFJV-UHFFFAOYSA-N 3-ethyl-2,4-dimethylheptane Chemical compound CCCC(C)C(CC)C(C)C OBCGEYFMJYXFJV-UHFFFAOYSA-N 0.000 description 1
- NKMJCVVUYDKHAV-UHFFFAOYSA-N 3-ethyl-2-methylheptane Chemical compound CCCCC(CC)C(C)C NKMJCVVUYDKHAV-UHFFFAOYSA-N 0.000 description 1
- MVLOWDRGPHBNNF-UHFFFAOYSA-N 3-ethyl-2-methylhexane Chemical compound CCCC(CC)C(C)C MVLOWDRGPHBNNF-UHFFFAOYSA-N 0.000 description 1
- OEYGTUAKNZFCDJ-UHFFFAOYSA-N 3-ethyloctane Chemical compound CCCCCC(CC)CC OEYGTUAKNZFCDJ-UHFFFAOYSA-N 0.000 description 1
- KYCZJIBOPKRSOV-UHFFFAOYSA-N 4-ethyl-2-methylhexane Chemical compound CCC(CC)CC(C)C KYCZJIBOPKRSOV-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- KOYGZROXUOTUEE-UHFFFAOYSA-N butane;but-1-ene Chemical compound CCCC.CCC=C KOYGZROXUOTUEE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- UNYSKUBLZGJSLV-UHFFFAOYSA-L calcium;1,3,5,2,4,6$l^{2}-trioxadisilaluminane 2,4-dioxide;dihydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].[OH-].[Ca+2].O=[Si]1O[Al]O[Si](=O)O1.O=[Si]1O[Al]O[Si](=O)O1 UNYSKUBLZGJSLV-UHFFFAOYSA-L 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229910052676 chabazite Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229910052675 erionite Inorganic materials 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 238000004858 feed analysis Methods 0.000 description 1
- 229910001657 ferrierite group Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0010433.1A GB0010433D0 (en) | 2000-04-28 | 2000-04-28 | Alkene oligomerization process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW527337B true TW527337B (en) | 2003-04-11 |
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Family Applications (1)
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|---|---|---|---|
| TW090113603A TW527337B (en) | 2000-04-28 | 2001-06-05 | Alkene oligomerization process |
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| EP (2) | EP1280747B1 (enExample) |
| JP (2) | JP5108194B2 (enExample) |
| KR (1) | KR100822318B1 (enExample) |
| CN (1) | CN1220658C (enExample) |
| AT (2) | ATE526300T1 (enExample) |
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| CA (1) | CA2405574C (enExample) |
| DE (1) | DE60126266T2 (enExample) |
| GB (1) | GB0010433D0 (enExample) |
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| TW (1) | TW527337B (enExample) |
| WO (1) | WO2001083407A1 (enExample) |
| ZA (1) | ZA200208524B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875899B2 (en) | 2001-02-01 | 2005-04-05 | Exxonmobil Chemical Patents Inc. | Production of higher olefins |
| US7183450B2 (en) | 2002-07-22 | 2007-02-27 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization |
| US7145049B2 (en) * | 2003-07-25 | 2006-12-05 | Catalytic Distillation Technologies | Oligomerization process |
| KR20070029127A (ko) * | 2003-12-18 | 2007-03-13 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 촉매화된 반응의 개선 방법 |
| US7588738B2 (en) | 2005-08-23 | 2009-09-15 | Exxonmobil Chemical Patents Inc. | Series catalyst beds |
| EP1948578B1 (en) * | 2005-09-30 | 2011-06-22 | ExxonMobil Chemical Patents Inc. | Oligomerization reaction |
| US7501548B2 (en) * | 2006-03-10 | 2009-03-10 | Exxonmobil Chemical Patents Inc. | Oligomerization of isobutene-containing feedstocks |
| CN101460428B (zh) * | 2006-06-07 | 2013-08-28 | 巴斯夫欧洲公司 | 共二聚烯烃的方法 |
| CN102482107B (zh) | 2009-08-28 | 2014-03-26 | 埃克森美孚化学专利公司 | 具有受控平均尺寸的mfs骨架类型分子筛的制备方法和应用 |
| US9394212B2 (en) | 2010-06-15 | 2016-07-19 | Basf Se | Process for the cooligomerization of olefins |
| WO2011157674A1 (de) | 2010-06-15 | 2011-12-22 | Basf Se | Verfahren zur co-oligomerisierung von olefinen |
| US9644159B2 (en) * | 2012-11-12 | 2017-05-09 | Uop Llc | Composition of oligomerate |
| CN109824802A (zh) * | 2012-12-21 | 2019-05-31 | 埃克森美孚化学专利公司 | 桥联的金属茂化合物、催化剂体系和使用它们的聚合方法 |
| SG11201702271VA (en) * | 2014-10-09 | 2017-04-27 | Basf Se | A process for the production of oligomerized olefins |
| KR102368268B1 (ko) | 2014-10-09 | 2022-02-28 | 바스프 에스이 | 흡착기 재생을 위한 생성물 회수 방법 |
| KR102368267B1 (ko) | 2014-10-09 | 2022-02-28 | 바스프 에스이 | 흡착기 재생을 위한 재순환 방법 |
| EA033601B1 (ru) | 2014-10-09 | 2019-11-08 | Basf Se | Способ регенерации адсорбера |
| EA033611B1 (ru) | 2014-10-09 | 2019-11-08 | Basf Se | Способ очистки органической композиции |
| ES2733399T3 (es) | 2014-10-09 | 2019-11-28 | Basf Se | Procedimiento de intercambio de calor para la regeneración de un adsorbedor |
| JP2018508557A (ja) * | 2015-03-20 | 2018-03-29 | エクソンモービル ケミカル パテンツ インコーポレイテッド | オレフィン含有炭化水素供給物をオリゴマー化生成物または水素化オリゴマー化生成物に変換する方法 |
| US11312669B2 (en) * | 2018-10-17 | 2022-04-26 | Exxonmobil Chemical Patents Inc. | Oligomerization of olefins |
| US11905227B2 (en) * | 2018-10-17 | 2024-02-20 | Exxonmobil Chemical Patents Inc. | Oligomerization of olefins |
| RU2709818C1 (ru) * | 2019-02-18 | 2019-12-23 | Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук | Способ получения олигомеров пент-1-ена в присутствии иерархического цеолита н-y |
| EP3990420A4 (en) * | 2019-06-27 | 2023-07-12 | GEVO, Inc. | OLIGOMERIZATION OF BIOLOGICALLY DERIVED OLEFINS THROUGH A CHABAZITE-TYPE ZEOLITE CATALYST |
| WO2021029377A1 (ja) * | 2019-08-09 | 2021-02-18 | 出光興産株式会社 | プロピレン４量体及びプロピレン４量体の製造方法 |
| JP2021028312A (ja) * | 2019-08-09 | 2021-02-25 | 出光興産株式会社 | プロピレン３量体及びプロピレン３量体の製造方法 |
| KR20220083701A (ko) * | 2019-10-18 | 2022-06-20 | 이데미쓰 고산 가부시키가이샤 | 프로필렌 올리고머의 제조 방법 |
| CN115196652A (zh) * | 2022-08-04 | 2022-10-18 | 南京工业大学 | 一种用于烯烃氧化的含钛沸石纳米片及其制备方法 |
| EP4455114A1 (de) | 2023-04-26 | 2024-10-30 | Evonik Oxeno GmbH & Co. KG | C8-kohlenwasserstoffzusammensetzungen und ein verfahren zu deren herstellung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3542171A1 (de) * | 1985-11-29 | 1987-06-04 | Basf Ag | Verfahren zur herstellung von diisobuten aus isobuten |
| JPH0669974B2 (ja) * | 1987-12-17 | 1994-09-07 | 三菱化成株式会社 | 可塑剤用アルコールの製造法 |
| DE69012295T2 (de) * | 1989-11-16 | 1995-01-05 | Mobil Oil Corp | Verfahren zur Qualitätserhöhung von Leichtolefinströmen. |
| GB9012725D0 (en) * | 1990-06-07 | 1990-08-01 | Exxon Chemical Patents Inc | Process for catalytic conversion of olefins |
| WO1993016020A2 (en) * | 1992-01-30 | 1993-08-19 | Exxon Chemical Patents Inc. | Alkene oligomerization |
| KR100364560B1 (ko) * | 1994-02-22 | 2003-02-17 | 엑손 케미칼 패턴츠 인코포레이티드 | 올리고머화및올리고머화를위한촉매 |
| ZA96178B (en) * | 1995-01-18 | 1997-06-30 | Exxon Chemical Patents Inc | Organic compounds and processes for their manufacture |
| GB9502342D0 (en) * | 1995-02-07 | 1995-03-29 | Exxon Chemical Patents Inc | Hydrocarbon treatment and catalyst therefor |
| JPH09268132A (ja) * | 1996-04-03 | 1997-10-14 | Mitsubishi Chem Corp | オレフィンの二量化法 |
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2000
- 2000-04-28 GB GBGB0010433.1A patent/GB0010433D0/en not_active Ceased
-
2001
- 2001-04-20 AU AU2001255533A patent/AU2001255533A1/en not_active Abandoned
- 2001-04-20 AT AT06077125T patent/ATE526300T1/de not_active IP Right Cessation
- 2001-04-20 KR KR1020027013815A patent/KR100822318B1/ko not_active Expired - Fee Related
- 2001-04-20 CA CA2405574A patent/CA2405574C/en not_active Expired - Fee Related
- 2001-04-20 CN CNB018086381A patent/CN1220658C/zh not_active Expired - Fee Related
- 2001-04-20 EP EP01928702A patent/EP1280747B1/en not_active Expired - Lifetime
- 2001-04-20 DE DE60126266T patent/DE60126266T2/de not_active Expired - Lifetime
- 2001-04-20 JP JP2001580842A patent/JP5108194B2/ja not_active Expired - Fee Related
- 2001-04-20 WO PCT/US2001/012891 patent/WO2001083407A1/en not_active Ceased
- 2001-04-20 EP EP06077125A patent/EP1772445B1/en not_active Revoked
- 2001-04-20 AT AT01928702T patent/ATE352533T1/de not_active IP Right Cessation
- 2001-04-26 MY MYPI20011966A patent/MY128446A/en unknown
- 2001-06-05 TW TW090113603A patent/TW527337B/zh active
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2002
- 2002-10-22 ZA ZA200208524A patent/ZA200208524B/en unknown
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- 2012-06-27 JP JP2012143980A patent/JP5572182B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1772445A1 (en) | 2007-04-11 |
| EP1280747B1 (en) | 2007-01-24 |
| JP2012229233A (ja) | 2012-11-22 |
| DE60126266D1 (de) | 2007-03-15 |
| WO2001083407A1 (en) | 2001-11-08 |
| EP1280747A1 (en) | 2003-02-05 |
| AU2001255533A1 (en) | 2001-11-12 |
| ATE526300T1 (de) | 2011-10-15 |
| KR100822318B1 (ko) | 2008-04-16 |
| DE60126266T2 (de) | 2007-10-31 |
| ATE352533T1 (de) | 2007-02-15 |
| ZA200208524B (en) | 2003-06-06 |
| CN1220658C (zh) | 2005-09-28 |
| MY128446A (en) | 2007-02-28 |
| CA2405574C (en) | 2010-07-06 |
| GB0010433D0 (en) | 2000-06-14 |
| JP5572182B2 (ja) | 2014-08-13 |
| KR20020089470A (ko) | 2002-11-29 |
| JP5108194B2 (ja) | 2012-12-26 |
| CN1437569A (zh) | 2003-08-20 |
| CA2405574A1 (en) | 2001-11-08 |
| EP1772445B1 (en) | 2011-09-28 |
| JP2003531877A (ja) | 2003-10-28 |
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